98830-20-7

Usage

General Description

25-hydroxydihydrotachysterol(2) is a synthetic form of vitamin D that is used as a therapeutic agent for the treatment of hypocalcemic conditions such as hypoparathyroidism and pseudo-hypoparathyroidism. It works by increasing the absorption of calcium and phosphorus in the intestines, as well as promoting the reabsorption of calcium in the kidneys. This helps to maintain proper levels of these minerals in the body, which are essential for bone health and overall bodily function. However, this chemical should be used with caution, as excessive levels of vitamin D can lead to hypercalcemia, which can have detrimental effects on health.

InChI:InChI=1/C28H46O2/c1-19-10-14-24(29)18-23(19)13-12-22-8-7-17-28(6)25(15-16-26(22)28)20(2)9-11-21(3)27(4,5)30/h9,11-13,19-21,24-26,29-30H,7-8,10,14-18H2,1-6H3/b11-9+,22-12+,23-13+/t19-,20+,21-,24-,25+,26-,28+/m0/s1

Upstream product

• 66774-71-8 Benzoic acid (1R,3aR,4S,7aR)-7a-methyl-1-((S)-1-methyl-2-oxo-ethyl)-octahydro-inden-4-yl ester 
• 66774-70-7 (8S,20S)-des-A,B-8-benzoyloxy-20-(hydroxymethyl)-pregnane 
• 142980-90-3 ethyl <(1'R,2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-1'-hydroxy-2'-methylcyclohexyl>ethanoate 
• 142980-88-9 ethyl <(1'R,2'S,5'S)-5'-acetoxy-1'-hydroxy-2'-methylcyclohexyl>ethanoate 
• 142980-87-8 ethyl <(1'R,2'S,5'S)-6-hydroperoxy-2',6-'dimethylbicyclo<3.2.1>-7'-oxaoctyl>ethanoate 
• 142980-89-0 ethyl <(1'R,2'S,5'S)-1',5-'dihydroxy-2'-methylcyclohexyl>ethanoate 
• 141277-81-8 (2E)-<2-<(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethyl>diphenylphosphine oxide 
• 100858-24-0 (22E,24S)-de-A,B-8β-(benzoyloxy)-25-<(methoxymethyl)oxy>ergost-22-ene 
• 100858-25-1 (22E,24S)-de-A,B-25-[(methoxymethyl)oxy]ergost-22-en-8β-ol 
• 142980-91-4 (2E)-ethyl <(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanoate 
• 142980-82-3 (2E)-ethyl <(2'S,5'S)-2'-methyl-5'-(1''-methylethenyl)cyclohexylidene>ethanoate 
• 142980-92-5 (2E)-2-<(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanol 
• 145260-95-3 [(2S,5S)-5-Hydroxy-2-methyl-cyclohex-(E)-ylidene]-acetic acid ethyl ester 
• 138079-57-9 Benzoic acid (1R,3aR,4S,7aR)-1-((E)-(1R,4S)-5-hydroxy-1,4,5-trimethyl-hex-2-enyl)-7a-methyl-octahydro-inden-4-yl ester 

Relevant academic research and scientific papers

A Convergent Approach to the Dihydrotachysterol Diene System. Application to the Synthesis of Dihydrotachysterol2 (DHT2), 25-Hydroxydihydrotachysterol2 (25-OH-DHT2), 10(R),19-dihydro-(5E)-3-epivitamin D2, and 25-Hydroxy-10(R),19-dihydro-(5E)-3-epivitamin D2

Total synthesis of A-ring fragments of 10(S),19-dihydrovitamins D and 10(R),19-dihydro-(5E)-epivitamins D from (+)-(S)-carvone and (-)-(R)-carvone is described.These fragments were used for convergent synthesis of dihydrotachysterol2 (DHT2), 25-hydroxydihydrotachysterol2, 10(R),19-dihydro-(5E)-3-epivitamin D2, and 25-hydroxy-10(R),19-dihydro-(5E)-3-epivitamin D2.

25-Hydroxydihydrotachysterol2. An innovative synthesis of a key metabolite of dihydrotachysterol2

A new synthesis of 25-hydroxydihydrotachysterol2 is described. The hydroxylated side-chain is constructed stereoselectively using a chiral Wittig reagent. The A-ring synthon is introduced utilising the Wittig-Horner method as developed by Lythgoe et al. The preparation of the metabolite is carried out in 18 steps.